3-naphthalen-1-yl-[1,2,4]oxadiazole-5-carboxylic acid hydrazide | 40019-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-naphthalen-1-yl-[1,2,4]oxadiazole-5-carboxylic acid hydrazide
• 英文别名: 5-Hydrazinocarbonyl-3-α-naphthyl-1,2,4-oxadiazole；5-Hydrazinocarbonyl-3-alpha-naphthyl-1,2,4-oxadiazole；3-naphthalen-1-yl-1,2,4-oxadiazole-5-carbohydrazide
• CAS: 40019-28-1
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: PRXRGKDRFNIECD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-naphthalen-1-yl-[1,2,4]oxadiazole-5-carboxylic acid hydrazide 、 4-氟苯基异硫氰酸酯 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到3-[[3-(naphthalen-1-yl)-[1,2,4]-oxadiazole-5-carbonyl]amino]-1-[4-fluorophenyl]thiourea
  参考文献：
  名称：

  Oxadiazole-carbonylaminothioureas as SIRT1 and SIRT2 Inhibitors

  摘要：

  A new inhibitor for human sirtuin type proteins I and 2 (SIRTI and SIRT2) was discovered through virtual database screening in search of new scaffolds. A series of compounds was synthesized based on the hit compound (3-[[3-(4-tert-butylphenyl) 1,2,4-oxadiazole5 -carbonyl I amino] -I - [3-(tri fluoromethy I)phenyl] thiourea). The most potent compound in the series was nearly as potent as the reference compound (6-chloro-2,3,4,9-tetrahydro-IH-carbazole-l-carboxamide).

  DOI：

  10.1021/jm800639h
• 作为产物：
  描述：

  3-naphthalen-1-yl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 3-naphthalen-1-yl-[1,2,4]oxadiazole-5-carboxylic acid hydrazide
  参考文献：
  名称：

  Mono- or disubstituted 1,2,4,oxadiazoles which are substituted by at

  摘要：

  1,2,4-氧代唑具有3-和5-位取代基，可以是氢原子，脂肪族，环脂族，芳基脂族，芳基或杂环基团，或者是具有-- CONR.sup.1 R.sup.2 公式的氨基甲酰基团，其中 R.sup.1 和 R.sup.2 可以相同也可以不同，可以是氢原子或脂肪族，环脂族，芳基脂族或芳基基团，或者与N原子结合形成杂环结构；前提是3-或5-位的至少一个取代基是N-取代的氨基甲酰基团。这一类化合物表现出抗微生物活性，尤其是抗病毒、抗寄生虫和抗菌活性。相应的氧代唑环也有描述，并且在氧代唑的制备中是有用的中间体。

  公开号：

  US03991067A1

文献信息

• Mono- or disubstituted 1,2,4,oxadiazoles which are substituted by at
  申请人：Glaxo Laboratories Limited

  公开号：US03991067A1

  公开（公告）日：1976-11-09

  1,2,4-Oxadiazoles having as 3- and 5-substituents a hydrogen atom, an aliphatic, cycloaliphatic, araliphatic, aryl or heterocyclic group, or a carbamoyl group of the formula -- CONR.sup.1 R.sup.2 where R.sup.1 & R.sup.2 which can be the same or different, are hydrogen atoms or aliphatic, cycloaliphatic, araliphatic or aryl groups or, taken with the N atom, a heterocvolic ring; provided that at least one of the 3- or 5-substituents is an N-substituted carbamoyl group. Antimicrobial activity, and particularly antiviral, antiparasitic and antibacterial activity is shown in this group. The corresponding oxadiazolins are also described and are useful intermediates in the preparation of the oxadiazoles.

  1,2,4-氧代唑具有3-和5-位取代基，可以是氢原子，脂肪族，环脂族，芳基脂族，芳基或杂环基团，或者是具有-- CONR.sup.1 R.sup.2 公式的氨基甲酰基团，其中 R.sup.1 和 R.sup.2 可以相同也可以不同，可以是氢原子或脂肪族，环脂族，芳基脂族或芳基基团，或者与N原子结合形成杂环结构；前提是3-或5-位的至少一个取代基是N-取代的氨基甲酰基团。这一类化合物表现出抗微生物活性，尤其是抗病毒、抗寄生虫和抗菌活性。相应的氧代唑环也有描述，并且在氧代唑的制备中是有用的中间体。
• Oxadiazole-carbonylaminothioureas as SIRT1 and SIRT2 Inhibitors
  作者：Tero Huhtiniemi、Tiina Suuronen、Valtteri M. Rinne、Carsten Wittekindt、Maija Lahtela-Kakkonen、Elina Jarho、Erik A. A. Wallén、Antero Salminen、Antti Poso、Jukka Leppänen

  DOI：10.1021/jm800639h

  日期：2008.8.1

  A new inhibitor for human sirtuin type proteins I and 2 (SIRTI and SIRT2) was discovered through virtual database screening in search of new scaffolds. A series of compounds was synthesized based on the hit compound (3-[[3-(4-tert-butylphenyl) 1,2,4-oxadiazole5 -carbonyl I amino] -I - [3-(tri fluoromethy I)phenyl] thiourea). The most potent compound in the series was nearly as potent as the reference compound (6-chloro-2,3,4,9-tetrahydro-IH-carbazole-l-carboxamide).